2-Phenyl-7-(4-pyridyl­methyl­amino)-1,2,4-triazolo[1,5-a][1,3,5]triazin-5(4H)-one

Dolzhenko, A.V.; Tan, G.K.; Dolzhenko, A.V.; Koh, L.L.; Chui, W.K.

doi:10.1107/S1600536810051032

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 1| January 2011| Pages o85-o86

https://doi.org/10.1107/S1600536810051032

Open

access

2-Phenyl-7-(4-pyridylmethylamino)-1,2,4-triazolo[1,5-a][1,3,5]triazin-5(4H)-one¹

Anton V. Dolzhenko,^a ^*‡ Geok Kheng Tan,^b Anna V. Dolzhenko,^c Lip Lin Koh ^b and Wai Keung Chui ^d

^aSchool of Pharmacy, Faculty of Health Sciences, Curtin University of Technology, GPO Box U1987, Perth 6845, Western Australia, Australia, ^bDepartment of Chemistry, Faculty of Science, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singapore, ^cPerm State Pharmaceutical Academy, 2 Polevaya Street, Perm 614990, Russian Federation, and ^dDepartment of Pharmacy, Faculty of Science, National University of Singapore, 18 Science Drive 4, Singapore 117543, Singapore
^*Correspondence e-mail: Anton.Dolzhenko@curtin.edu.au

(Received 26 November 2010; accepted 6 December 2010; online 11 December 2010)

In the title compound, C₁₆H₁₃N₇O, the 1,2,4-triazolo[1,5-a][1,3,5]triazine heterocyclic system is essentially planar (r.m.s. deviation = 0.0375 Å). The attached benzene ring lies almost in the mean plane of 1,2,4-triazolo[1,5-a][1,3,5]triazine [dihedral angle = 1.36 (23)°], while the pyridine ring is turned out of this plane by the aminomethyl bridge [dihedral angle = 69.22 (9)°]. The amino group H atom is involved in intramolecular hydrogen bonding with a triazole N atom. In the crystal, molecules are connected via C(=O)NH⋯N hydrogen bonds into C(11) chains parallel to [100]. The amino group H atom acts as a hydrogen-bond donor, forming an NH⋯O=C hydrogen bond with the carbonyl O atom, which links the molecules into C(6) chains running along [011] and [01 $[\overline{1}]$ ].

Related literature

For review on the synthesis and biological activity of 1,2,4-triazolo[1,5-a][1,3,5]triazines, see: Dolzhenko et al. (2006 ). For our work on the synthesis, crystal structure studies and biological activity of 1,2,4-triazolo[1,5-a][1,3,5]triazine, see: Dolzhenko et al. (2007a ,b , 2008 ). For graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995 ). For a related structure, see: Dolzhenko et al. (2011 ).

Experimental

Crystal data

C₁₆H₁₃N₇O
M_r = 319.33
Orthorhombic, P n a 2₁
a = 22.142 (8) Å
b = 11.016 (4) Å
c = 5.992 (2) Å
V = 1461.5 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.58 × 0.36 × 0.04 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ) T_min = 0.945, T_max = 0.996
9607 measured reflections
1830 independent reflections
1530 reflections with I > 2σ(I)
R_int = 0.088

Refinement

R[F² > 2σ(F²)] = 0.067
wR(F²) = 0.145
S = 1.19
1830 reflections
225 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5N⋯N7ⁱ	0.90 (4)	1.89 (4)	2.782 (5)	173 (4)
N6—H6N⋯O1ⁱⁱ	0.95 (6)	1.96 (5)	2.735 (5)	137 (4)
N6—H6N⋯N1	0.95 (6)	2.31 (5)	2.813 (5)	112 (4)
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ ; (ii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810051032/hg2761sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810051032/hg2761Isup2.hkl

checkCIF report

Comment top

The 1,2,4-triazolo[1,5-a]triazines are 5-azaisosters of the purine heterocyclic system that carries a bridge nitrogen atom. They have been shown to possess a variety of promising biological effects (Dolzhenko et al., 2006). In continuation of our works on the synthesis and structural investigations of 1,2,4-triazolo[1,5-a][1,3,5]triazines (Dolzhenko et al., 2007a,b; Dolzhenko et al., 2008), we report herein molecular and crystal structure of 2-phenyl-7-(4-pyridylmethylamino)-1,2,4-triazolo[1,5-a][1,3,5]triazin-5-one, C₁₆H₁₃N₇O. (Fig. 1 & 2).

The 1,2,4-triazolo[1,5-a][1,3,5]triazine heterocyclic system is essentially planar with a r.m.s. deviation of 0.0375 Å. The phenyl ring lies practically in the plane of the 1,2,4-triazolo[1,5-a][1,3,5]triazine core (with a small dihedral angle of 1.36 (23)° between the mean planes). The amino group nitrogen atom N6 is located 0.2246 (50) Å above the 1,2,4-triazolo[1,5-a][1,3,5]triazine mean plane. The pyridine ring is turned out of this plane by twisting of the aminomethyl bridge [C3—N6—C11—C14 torsion angle is 118.50 (40)°]. This results in a dihedral angle of 69.22 (9)° between the 1,2,4-triazolo[1,5-a][1,3,5]triazine and pyridine mean planes. The amino group N6H hydrogen atom acts as a hydrogen donor in the NH···N intramolecular hydrogen bonding with the triazole N1 atom.

In the crystal, molecules form a three dimensional network of chains. The C(11) chains (Bernstein et al., 1995) parallel to a [100] axis consist of the molecules linked via the CONH···N hydrogen bonds between the triazine N6H atom and the N7 atom of pyridine ring. The C(6) chains running along [011] and [011] directions are made of the molecules connected via the NH···O═C contacts between the N6—H amino group acting as a hydrogen donor and the carbonyl group O1 atom in the role of a hydrogen acceptor.

Related literature top

For review on the synthesis and biological activity of 1,2,4-triazolo[1,5-a][1,3,5]triazines, see: Dolzhenko et al. (2006). For our work on the synthesis, crystal structure studies and biological activity of 1,2,4-triazolo[1,5-a][1,3,5]triazine, see: Dolzhenko et al. (2007a,b, 2008). For the graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995). For a related structure, see: Dolzhenko et al. (2011).

Experimental top

7-Methylthio-2-phenyl-1,2,4-triazole[1,5-a][1,3,5]triazin-5-one (0.52 g, 2 mmol) was added to a solution of 4-pyridylmethylamine (0.32 g, 3 mmol) in DMF (5 ml) and the mixture was heated at 70–80°C with stirring for 6 h. After cooling, ice cold water (40 ml) was added and the product was filtered and recrystalized from methanol. Yield: 0.56 g (87%), m.p. 567 K.

Structure description top

For review on the synthesis and biological activity of 1,2,4-triazolo[1,5-a][1,3,5]triazines, see: Dolzhenko et al. (2006). For our work on the synthesis, crystal structure studies and biological activity of 1,2,4-triazolo[1,5-a][1,3,5]triazine, see: Dolzhenko et al. (2007a,b, 2008). For the graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995). For a related structure, see: Dolzhenko et al. (2011).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of 2-phenyl-7-(4-pyridylmethylamino)-1,2,4-triazolo[1,5-a][1,3,5]triazin-5-one showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Crystal packing in the cell (view along axis c).

2-Phenyl-7-(4-pyridylmethylamino)-1,2,4- triazolo[1,5-a][1,3,5]triazin-5(4H)-one top

Crystal data top

C₁₆H₁₃N₇O	D_x = 1.451 Mg m⁻³
M_r = 319.33	Melting point: 567 K
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 569 reflections
a = 22.142 (8) Å	θ = 2.6–21.1°
b = 11.016 (4) Å	µ = 0.10 mm⁻¹
c = 5.992 (2) Å	T = 100 K
V = 1461.5 (9) Å³	Thin plate, colourless
Z = 4	0.58 × 0.36 × 0.04 mm
F(000) = 664

Data collection top

Bruker SMART APEX CCD diffractometer	1830 independent reflections
Radiation source: fine-focus sealed tube	1530 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.088
φ and ω scans	θ_max = 27.5°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −25→28
T_min = 0.945, T_max = 0.996	k = −14→14
9607 measured reflections	l = −7→7

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.145	H atoms treated by a mixture of independent and constrained refinement
S = 1.19	w = 1/[σ²(F_o²) + (0.0695P)² + 0.135P] where P = (F_o² + 2F_c²)/3
1830 reflections	(Δ/σ)_max < 0.001
225 parameters	Δρ_max = 0.35 e Å⁻³
1 restraint	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₆H₁₃N₇O	V = 1461.5 (9) Å³
M_r = 319.33	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 22.142 (8) Å	µ = 0.10 mm⁻¹
b = 11.016 (4) Å	T = 100 K
c = 5.992 (2) Å	0.58 × 0.36 × 0.04 mm

Data collection top

Bruker SMART APEX CCD diffractometer	1830 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	1530 reflections with I > 2σ(I)
T_min = 0.945, T_max = 0.996	R_int = 0.088
9607 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	1 restraint
wR(F²) = 0.145	H atoms treated by a mixture of independent and constrained refinement
S = 1.19	Δρ_max = 0.35 e Å⁻³
1830 reflections	Δρ_min = −0.27 e Å⁻³
225 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.83275 (13)	0.3791 (3)	0.1382 (6)	0.0251 (8)
N1	0.78903 (15)	0.0671 (3)	0.7906 (7)	0.0191 (8)
N2	0.88088 (15)	0.1634 (3)	0.7854 (7)	0.0186 (8)
N3	0.79295 (15)	0.1475 (3)	0.6125 (6)	0.0174 (8)
N4	0.76558 (15)	0.2401 (3)	0.2791 (7)	0.0187 (8)
N5	0.86084 (16)	0.2819 (3)	0.4502 (6)	0.0186 (8)
H5N	0.900 (2)	0.301 (4)	0.429 (8)	0.018 (12)*
N6	0.70697 (15)	0.0862 (3)	0.4338 (6)	0.0201 (8)
H6N	0.712 (2)	0.025 (5)	0.544 (10)	0.039 (15)*
N7	0.48227 (17)	0.1748 (3)	0.3615 (7)	0.0236 (8)
C1	0.84184 (19)	0.0814 (4)	0.8851 (8)	0.0177 (9)
C2	0.84876 (18)	0.2014 (3)	0.6159 (7)	0.0166 (9)
C3	0.75455 (18)	0.1596 (3)	0.4347 (7)	0.0175 (9)
C4	0.81929 (18)	0.3037 (4)	0.2826 (8)	0.0183 (9)
C5	0.85949 (19)	0.0149 (4)	1.0875 (7)	0.0199 (9)
C6	0.9147 (2)	0.0359 (4)	1.1868 (8)	0.0264 (10)
H6	0.9422	0.0910	1.1197	0.032*
C7	0.9305 (2)	−0.0226 (4)	1.3837 (9)	0.0329 (12)
H7	0.9687	−0.0080	1.4504	0.040*
C8	0.8899 (3)	−0.1029 (4)	1.4827 (9)	0.0358 (13)
H8	0.9001	−0.1420	1.6190	0.043*
C9	0.8347 (2)	−0.1258 (4)	1.3827 (9)	0.0317 (11)
H9	0.8075	−0.1820	1.4492	0.038*
C10	0.8187 (2)	−0.0678 (4)	1.1872 (7)	0.0241 (10)
H10	0.7806	−0.0832	1.1201	0.029*
C11	0.66773 (18)	0.0743 (4)	0.2433 (7)	0.0206 (10)
H11A	0.6682	−0.0112	0.1928	0.025*
H11B	0.6838	0.1248	0.1202	0.025*
C12	0.49957 (19)	0.1204 (4)	0.1724 (8)	0.0242 (10)
H12	0.4698	0.1032	0.0627	0.029*
C13	0.55916 (19)	0.0879 (4)	0.1287 (8)	0.0218 (10)
H13	0.5698	0.0500	−0.0082	0.026*
C14	0.60260 (19)	0.1119 (4)	0.2896 (8)	0.0187 (9)
C15	0.58514 (19)	0.1699 (4)	0.4811 (8)	0.0211 (9)
H15	0.6141	0.1894	0.5923	0.025*
C16	0.5247 (2)	0.2002 (4)	0.5120 (8)	0.0245 (10)
H16	0.5133	0.2406	0.6456	0.029*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0245 (16)	0.0180 (14)	0.0328 (19)	0.0027 (12)	0.0069 (15)	0.0101 (15)
N1	0.0230 (18)	0.0146 (17)	0.0196 (17)	−0.0022 (14)	0.0025 (17)	0.0034 (15)
N2	0.0180 (18)	0.0137 (16)	0.0240 (18)	0.0024 (13)	0.0013 (16)	−0.0026 (16)
N3	0.0192 (17)	0.0115 (16)	0.022 (2)	−0.0018 (13)	0.0019 (15)	0.0038 (15)
N4	0.0214 (18)	0.0105 (16)	0.0241 (19)	0.0029 (13)	0.0030 (16)	0.0038 (16)
N5	0.0176 (18)	0.0123 (17)	0.026 (2)	−0.0018 (13)	0.0039 (16)	0.0019 (16)
N6	0.0173 (18)	0.0153 (17)	0.028 (2)	0.0014 (13)	−0.0002 (17)	0.0088 (17)
N7	0.0244 (19)	0.0164 (17)	0.030 (2)	0.0040 (15)	0.0003 (17)	0.0025 (17)
C1	0.020 (2)	0.0154 (19)	0.018 (2)	0.0020 (16)	0.0032 (18)	−0.0025 (18)
C2	0.018 (2)	0.0092 (17)	0.023 (2)	0.0000 (15)	0.0027 (18)	−0.0024 (18)
C3	0.0169 (19)	0.0130 (19)	0.023 (2)	0.0054 (15)	0.0042 (18)	−0.0031 (18)
C4	0.020 (2)	0.0132 (19)	0.021 (2)	0.0056 (15)	0.0000 (19)	0.0011 (19)
C5	0.025 (2)	0.0156 (19)	0.019 (2)	0.0070 (17)	0.0032 (19)	−0.0046 (18)
C6	0.035 (3)	0.022 (2)	0.023 (2)	0.0087 (19)	−0.003 (2)	−0.005 (2)
C7	0.044 (3)	0.024 (2)	0.031 (3)	0.014 (2)	−0.013 (2)	−0.004 (2)
C8	0.062 (4)	0.027 (2)	0.018 (2)	0.022 (2)	−0.006 (2)	−0.002 (2)
C9	0.049 (3)	0.020 (2)	0.026 (2)	0.012 (2)	0.006 (2)	0.004 (2)
C10	0.031 (2)	0.017 (2)	0.024 (2)	0.0049 (17)	0.005 (2)	−0.002 (2)
C11	0.023 (2)	0.0137 (18)	0.025 (3)	0.0005 (17)	0.0012 (19)	−0.0021 (19)
C12	0.022 (2)	0.022 (2)	0.028 (3)	−0.0003 (18)	0.003 (2)	0.000 (2)
C13	0.024 (2)	0.016 (2)	0.025 (2)	−0.0008 (17)	−0.001 (2)	−0.0008 (19)
C14	0.023 (2)	0.0082 (17)	0.025 (2)	0.0013 (15)	0.003 (2)	0.0068 (18)
C15	0.024 (2)	0.015 (2)	0.025 (2)	−0.0018 (17)	−0.004 (2)	−0.0004 (19)
C16	0.034 (3)	0.0121 (19)	0.028 (2)	0.0022 (18)	0.003 (2)	−0.0026 (19)

Geometric parameters (Å, º) top

O1—C4	1.236 (5)	C6—C7	1.389 (7)
N1—C1	1.309 (5)	C6—H6	0.9500
N1—N3	1.389 (5)	C7—C8	1.394 (8)
N2—C2	1.308 (6)	C7—H7	0.9500
N2—C1	1.386 (5)	C8—C9	1.384 (8)
N3—C3	1.370 (5)	C8—H8	0.9500
N3—C2	1.371 (5)	C9—C10	1.381 (7)
N4—C3	1.310 (5)	C9—H9	0.9500
N4—C4	1.380 (5)	C10—H10	0.9500
N5—C2	1.358 (5)	C11—C14	1.526 (6)
N5—C4	1.383 (6)	C11—H11A	0.9900
N5—H5N	0.90 (4)	C11—H11B	0.9900
N6—C3	1.328 (5)	C12—C13	1.392 (6)
N6—C11	1.441 (5)	C12—H12	0.9500
N6—H6N	0.95 (6)	C13—C14	1.387 (6)
N7—C16	1.332 (6)	C13—H13	0.9500
N7—C12	1.338 (6)	C14—C15	1.369 (7)
C1—C5	1.470 (6)	C15—C16	1.392 (6)
C5—C6	1.379 (6)	C15—H15	0.9500
C5—C10	1.415 (6)	C16—H16	0.9500

C1—N1—N3	101.5 (3)	C6—C7—H7	120.2
C2—N2—C1	101.8 (3)	C8—C7—H7	120.2
C3—N3—C2	121.9 (4)	C9—C8—C7	120.0 (5)
C3—N3—N1	128.4 (3)	C9—C8—H8	120.0
C2—N3—N1	108.7 (3)	C7—C8—H8	120.0
C3—N4—C4	119.6 (4)	C10—C9—C8	120.6 (5)
C2—N5—C4	120.9 (4)	C10—C9—H9	119.7
C2—N5—H5N	116 (3)	C8—C9—H9	119.7
C4—N5—H5N	120 (3)	C9—C10—C5	119.5 (4)
C3—N6—C11	122.5 (4)	C9—C10—H10	120.2
C3—N6—H6N	110 (3)	C5—C10—H10	120.2
C11—N6—H6N	123 (3)	N6—C11—C14	113.7 (4)
C16—N7—C12	117.7 (4)	N6—C11—H11A	108.8
N1—C1—N2	116.7 (4)	C14—C11—H11A	108.8
N1—C1—C5	122.3 (4)	N6—C11—H11B	108.8
N2—C1—C5	121.0 (4)	C14—C11—H11B	108.8
N2—C2—N5	132.0 (4)	H11A—C11—H11B	107.7
N2—C2—N3	111.3 (4)	N7—C12—C13	123.1 (4)
N5—C2—N3	116.7 (4)	N7—C12—H12	118.5
N4—C3—N6	123.9 (4)	C13—C12—H12	118.5
N4—C3—N3	120.3 (4)	C14—C13—C12	118.5 (4)
N6—C3—N3	115.9 (4)	C14—C13—H13	120.7
O1—C4—N4	122.6 (4)	C12—C13—H13	120.7
O1—C4—N5	117.7 (4)	C15—C14—C13	118.4 (4)
N4—C4—N5	119.7 (4)	C15—C14—C11	123.1 (4)
C6—C5—C10	119.5 (4)	C13—C14—C11	118.5 (4)
C6—C5—C1	120.5 (4)	C14—C15—C16	119.7 (4)
C10—C5—C1	120.0 (4)	C14—C15—H15	120.2
C5—C6—C7	120.8 (5)	C16—C15—H15	120.2
C5—C6—H6	119.6	N7—C16—C15	122.6 (4)
C7—C6—H6	119.6	N7—C16—H16	118.7
C6—C7—C8	119.6 (5)	C15—C16—H16	118.7

C1—N1—N3—C3	169.6 (4)	C2—N5—C4—N4	−2.1 (6)
C1—N1—N3—C2	0.9 (4)	N1—C1—C5—C6	−177.5 (4)
N3—N1—C1—N2	−0.4 (5)	N2—C1—C5—C6	2.2 (6)
N3—N1—C1—C5	179.3 (4)	N1—C1—C5—C10	−0.2 (6)
C2—N2—C1—N1	−0.2 (5)	N2—C1—C5—C10	179.5 (4)
C2—N2—C1—C5	−180.0 (4)	C10—C5—C6—C7	−0.3 (6)
C1—N2—C2—N5	−179.3 (4)	C1—C5—C6—C7	177.1 (4)
C1—N2—C2—N3	0.8 (4)	C5—C6—C7—C8	−0.4 (6)
C4—N5—C2—N2	177.7 (4)	C6—C7—C8—C9	1.3 (7)
C4—N5—C2—N3	−2.5 (6)	C7—C8—C9—C10	−1.4 (7)
C3—N3—C2—N2	−170.7 (3)	C8—C9—C10—C5	0.6 (7)
N1—N3—C2—N2	−1.1 (4)	C6—C5—C10—C9	0.2 (6)
C3—N3—C2—N5	9.4 (5)	C1—C5—C10—C9	−177.2 (4)
N1—N3—C2—N5	179.0 (3)	C3—N6—C11—C14	−118.5 (4)
C4—N4—C3—N6	−173.5 (4)	C16—N7—C12—C13	1.1 (6)
C4—N4—C3—N3	6.8 (5)	N7—C12—C13—C14	0.6 (7)
C11—N6—C3—N4	10.2 (6)	C12—C13—C14—C15	−2.0 (6)
C11—N6—C3—N3	−170.1 (3)	C12—C13—C14—C11	179.0 (4)
C2—N3—C3—N4	−11.9 (5)	N6—C11—C14—C15	10.2 (5)
N1—N3—C3—N4	−179.2 (4)	N6—C11—C14—C13	−170.8 (4)
C2—N3—C3—N6	168.4 (4)	C13—C14—C15—C16	1.6 (6)
N1—N3—C3—N6	1.0 (6)	C11—C14—C15—C16	−179.4 (4)
C3—N4—C4—O1	178.6 (4)	C12—N7—C16—C15	−1.5 (6)
C3—N4—C4—N5	0.0 (6)	C14—C15—C16—N7	0.1 (6)
C2—N5—C4—O1	179.1 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5N···N7ⁱ	0.90 (4)	1.89 (4)	2.782 (5)	173 (4)
N6—H6N···O1ⁱⁱ	0.95 (6)	1.96 (5)	2.735 (5)	137 (4)
N6—H6N···N1	0.95 (6)	2.31 (5)	2.813 (5)	112 (4)

Symmetry codes: (i) x+1/2, −y+1/2, z; (ii) −x+3/2, y−1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₃N₇O
M_r	319.33
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	100
a, b, c (Å)	22.142 (8), 11.016 (4), 5.992 (2)
V (Å³)	1461.5 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.58 × 0.36 × 0.04

Data collection
Diffractometer	Bruker SMART APEX CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001)
T_min, T_max	0.945, 0.996
No. of measured, independent and observed [I > 2σ(I)] reflections	9607, 1830, 1530
R_int	0.088
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.145, 1.19
No. of reflections	1830
No. of parameters	225
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.27

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5N···N7ⁱ	0.90 (4)	1.89 (4)	2.782 (5)	173 (4)
N6—H6N···O1ⁱⁱ	0.95 (6)	1.96 (5)	2.735 (5)	137 (4)
N6—H6N···N1	0.95 (6)	2.31 (5)	2.813 (5)	112 (4)

Symmetry codes: (i) x+1/2, −y+1/2, z; (ii) −x+3/2, y−1/2, z+1/2.

Footnotes

¹Fused heterocyclic systems with s-triazine ring. Part 17. For part 16, see Dolzhenko et al. (2011).

‡Thomson Reuters ResearcherID: B-1130-2008.

Acknowledgements

This work was supported by the School of Pharmacy, Curtin University of Technology and the National Medical Research Council, Singapore (NMRC/NIG/0019/2008).

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N. L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2001). SMART and SAINT. Bruker AXS GmbH, Karlsruhe, Germany. Google Scholar
Dolzhenko, A. V., Dolzhenko, A. V. & Chui, W. K. (2006). Heterocycles, 68, 1723–1759. CAS Google Scholar
Dolzhenko, A. V., Dolzhenko, A. V. & Chui, W. K. (2007a). Heterocycles, 71, 429–436. CAS Google Scholar
Dolzhenko, A. V., Dolzhenko, A. V. & Chui, W. K. (2007b). Tetrahedron, 63, 12888–12895. Web of Science CrossRef CAS Google Scholar
Dolzhenko, A. V., Pastorin, G., Dolzhenko, A. V. & Chui, W. K. (2008). Tetrahedron Lett. 49, 7180–7183. Web of Science CrossRef CAS Google Scholar
Dolzhenko, A. V., Tan, G. K., Dolzhenko, A. V., Koh, L. L. & Chui, W. K. (2011). Acta Cryst. E67, o83–o84. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2001). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.